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192619

Sigma-Aldrich

Tiglic aldehyde

≥96%

Sinónimos:

(E)-2-Methylbut-2-enal, trans-2,3-Dimethylacrolein, trans-2-Methyl-2-butenal, Tiglinaldehyde

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About This Item

Fórmula lineal:
CH3CH=C(CH3)CHO
Número de CAS:
497-03-0
Peso molecular:
84.12
Beilstein/REAXYS Number:
1698207
MDL number:
MFCD00006977
UNSPSC Code:
12352100
PubChem Substance ID:
24851554
NACRES:
NA.22

assay

≥96%

form

liquid

refractive index

n20/D 1.448 (lit.)

bp

116-119 °C/752 mmHg (lit.)

density

0.869 g/mL at 20 °C
0.871 g/mL at 25 °C (lit.)

SMILES string

C\C=C(/C)C=O

InChI

1S/C5H8O/c1-3-5(2)4-6/h3-4H,1-2H3/b5-3+

InChI key

ACWQBUSCFPJUPN-HWKANZROSA-N

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Application

Tiglic aldehyde was used in the concise total synthesis of 7-demethylpiericidin A1. It was used as starting reagent during the synthesis of:
  • alkyl-branched tetraene hydrocarbons, pheromone component for dried fruit beetle
  • E,E-2,4-dimethyl-2,4-hexa dienal, volatile constituents of the defensive secretions of Leiobunum nigripalpi
  • 4-methyl-2,4-hexadiene-1-ol

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

69.8 °F - closed cup

flash_point_c

21 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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trans-2,3-Dimethylacrylic acid 98%

Sigma-Aldrich

T35203

trans-2,3-Dimethylacrylic acid

trans-2-Methyl-2-butenoic acid ≥99%, FG

Sigma-Aldrich

W359904

trans-2-Methyl-2-butenoic acid

Synthesis of nitidulid beetle pheromones: alkyl-branched tetraene hydrocarbons.
Bartelt RJ, et al.
Journal of Agricultural and Food Chemistry, 38(12), 2192-2196 (1990)
Synthesis of 1, 2-and 1, 4-disubstituted tricarbonyl (pentadienyl) iron (+ 1) cations and reactions with heteroatom nucleophiles.
Donaldson WA, et al
Organometallics, 12(4), 1174-1179 (1993)
T H Jones et al.
Proceedings of the National Academy of Sciences of the United States of America, 74(2), 419-422 (1977-02-01)
Analyses of the chief volatile constituents of the defensive secretions of three oplionids were carried out. Leiobunum nigripalpi produces three closely related C7 compounds: E-4-methyl-4-hexen-3-one(I), 4-methylhexan-3-one(II), and 4-methylhexan-3-ol(III), along with E-4-methyl-4-hepten-3-one(IV), E,E-2,4-dimethylhexa-2,4-dienal(IX), and a minor, unidentified component. L. leiopenis secretion
Katie A Keaton et al.
Journal of the American Chemical Society, 128(2), 408-409 (2006-01-13)
A concise total synthesis of 7-demethylpiericidin A1 has been completed. The synthesis features a titanium(II)-mediated cyclization of a (silyloxy)enyne as the key step and proceeds in nine steps from tiglic aldehyde.
Hasmik Grigoryan et al.
Carcinogenesis, 39(5), 661-668 (2018-03-15)
Although benzene has long been recognized as a cause of human leukemia, the mechanism by which this simple molecule causes cancer has been problematic. A complicating factor is benzene metabolism, which produces many reactive intermediates, some specific to benzene and
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